The disaccharide trehalose is involved in stress response in many organisms. However, in plants, its precise role remains unclear, although some data indicate that trehalose has a protective role during abiotic stresses. By contrast, some trehalose metabolism mutants exhibit growth aberrations, revealing potential negative effects on plant physiology. Contradictory effects also appear under biotic stress conditions. Specifically, trehalose is essential for the infectivity of several pathogens but at the same time elicits plant defense. Here, we argue that trehalose should not be regarded only as a protective sugar but rather like a double-faced molecule and that further investigation is required to elucidate its exact role in stress tolerance in plants.